Comedian Josh Gondelman Might Be Nicest Man In Comedy

Nice guys are supposed to finish last, but comedy writer and stand-up comedian Josh Gondelman seems to defy that aphorism.

Frequently referred to as "the nicest man in comedy," the Boston native, and current Brooklyn, New York, resident, must feel more than nice as his career in the cutthroat entertainment business is clearly on the rise.

Gondelman's comedy CV remains impressive.

He earned his stripes in the comedy world after years of working as a stand-up comedian, freelance writer and author. Many took note of his writing talents, but even more did so when he co-created the Modern Seinfield Twitter account, which posits "What if Seinfeld were still on the air?" and presents sitcom premises and dialogue in tweet form. The ensuing social-media frenzy opened important doors, and Gondleman went on to work as a web producer and writer for "Last Week Tonight with John Oliver" on HBO for five years. Earlier this year, he moved over to become a writer and producer for late-night talk show "Desus & Mero" on Showtime.

With Gondelman's new stand-up album, "Dancing On A Weeknight," arriving Friday, "BETA" host Doug Gordon sought to ask him the crucial questions about his new album, his comedic voice, his high-profile gigs and just how he got the rep as the "nicest man in comedy."

The interview has been edited for brevity and clarity.

Doug Gordon: Where does the title of your new album, "Dancing On A Weeknight," come from?

Josh Gondelman: It's fun, but it's not outrageous in any way. I think ... it's kind of like a mostly wholesome, good time that you know maybe it leads into other things. Maybe it doesn't, but it's the idea of just like dancing on a weeknight is just like slightly outside of what you're supposed to do.

DG: How (has) your comedic voice developed over the years that you've been doing stand-up?

JG: I think it's gotten a little closer to how I see the world and I think I've gotten better able to be more like myself and more like the way I can be funny offstage while I'm on stage. I'm also doing less saying stuff because it's funny and gets a laugh and more saying stuff that's like, "Oh, I'd like to talk about this like this is an idea or an experience I have." And I wonder if I can put that through some kind of filter and turn it into comedy rather than I have this thought I said it. People laugh at it so it stays in the hour.

DG:The Village Voice, in one piece in a story about you, they describe you as a high-functioning neurotic? What does that mean? First of all, do you agree with that description?

JG: It's a very sweet and very fun way to describe me. I don't think I'm that neurotic.

Drew Grant at the Observer, years ago, when I co-wrote a book ... described me as, I think, ... as a pathological sweetheart. That is something that's always stuck in my mind where it's not that I am. It's not that I'm neurotic and functioning in spite of it, it's that my specific pathology has me locked into unfailing politeness, even when there is no reason to be polite and kind of unflagging cheeriness even when there's no reason to be cheerful.

DG:You're frequently described as the "nicest man in comedy" as well?

JG: That's very kind. And it's very nice to have that reputation. And I try to be nice. I think there are other very nice people, but I think I might not be the nicest, but I'm definitely very friendly, and I think friendly reads as nice when, kind of quiet and supportive, otherwise doesn't outwardly play is as nice all the time, especially when someone's act is a little greedier than mine.

And I think that because my act is also very cheerful and pleasant, that I reaped the benefits of that, conflate that with who I am offstage, which is like very close to the same thing.

DG: You and your friend Jack Moore came up with (what) was one of the most brilliant Twitter accounts ever back around 2012, and I'm not using hyperbole here. It's called Modern Seinfeld. Can you tell me about Modern Seinfeld?

JG: The premise was: What would be little plot threads if "Seinfeld" were still on the air? And just because so much of it was based in little etiquette customs and kind of technological snafus, like answering machine messages. And there was just so much of it that felt like if you lived through that time, it still plays. But it's like answering machines are such a specific thing that I don't know if a 14-year-old in the year 2019 gets the visceral feeling of, "I have to go home and erase this answering machine message because someone else will hear my voicemail."

And so I had tweeted a couple of things about Modern Seinfeld plotlines just from my own account. And Jack was like, 'You know, this could really be a thing.'

And so he staked out the handle and then we just kind of wrote that for a while. And it was very, again, very flattering that people liked it and it was really fun. But also we were like standing on the shoulders of giants in terms of "Seinfeld" is one of the best TV shows of all time ... So it was very thrilling that people thought that we were doing a good facsimile or extension of this like beloved TV institution.

Kramer hosts a "non-recorded" podcast. K:"It's just like a podcast, but no microphones." J:"So a conversation?" K:"You don't get it Jerry!"

DG: You managed to parlay your Twitter account into a comedy career. How did you do that?

JG: I'd already been doing stand-up for a number of years ... when the Twitter account exploded. Basically overnight, we got these (opportunities). People wanted to talk to us about things. They wanted to hear pitches for stuff. And I was like slightly unprepared. I didn't have a lot of scripts ready to go. "Hey, staff me on the show. Here's my writing sample."

So, I did after the Modern Seinfeld Twitter kind of blew up, I applied to writing jobs basically for a year. Thanks to ... a little bit of industry attention and validation that came from that. And I did a little work for "Billy on the Street" the summer of 2013 and then I got hired at the beginning of 2014 to do the digital social stuff for "Last Week Tonight With John Oliver" as the show (was) launching. And I did that for a year and then was moved over mostly to write for the show.

I was there for half a decade, which is like truly wild to me. I never thought that that could happen. When I started doing standup, (I) did not ever really think "Oh, I'm going to get to work at a show that I am really proud of with people are really great and for such a sustained period of time." I would watch "The Daily Show" in high school and college and think, "Man, what a cool thing that is." And then I got to work in that field.

DG: Can you point to a particular moment that you created for "Last Week Tonight With John Oliver" that you're particularly proud of?

JG: Oh man, let me think. I really like the like dumbest stuff because John, I think, because he's so rigorous about what he says on the air and so scrupulous about making sure ... he's expressing exactly what he wants to express. And I think his accent lends him an additional gravitas.

He's an incredibly funny comedian and comedy writer so ... it was really fun to write jokes and watch him deliver and kill in the room. And then, immediately hush the crowd because he had four words to say very quickly.

DG: You now work with "Desus & Mero." Why did you choose to leave "Last Week Tonight" to go work with "Deus & Mero?"

JG: It was just a really exciting opportunity that came up to work on a new show that was launching with people that I think are so funny and it just felt very different in terms of what the show would be like and what ... their comedic voice (is). And so, I was really excited to move and have kind of different responsibilities at a different show that I also felt really psyched about.

I wasn't like clawing at the walls to leave. I would have been very happy coming back for another season. But right as the season was ending, I got asked to interview for the show and it just seemed like a really fun next thing to work on. And I'm really enjoying it and the guys are so funny. And it's just again going from like one super, over-the-moon dream job to another one, which has been a great privilege.

DG:Did you have to develop a different comedic voice and kind of comedic timing to work on the show?

JG: It is very different. It's mostly structurally different, where instead of writing as many super, precise jokes, it's a lot about writing incredibly clear clean copy that leads "Desus & Mero" into the kind of improvisation they're doing. And then it's writing a lot more sketches, pitching more silly ideas to do in the field, "man on the street" stuff.

And that was one of the things that I think was appealing to me was that I wasn't going to be moving and writing the same kind of show in a different voice, but it would be like fully flexing different muscles or like developing different muscles. And I'm very I'm like really enjoying learning how to build up those skills to.

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